Wanting to share some of the best of Italy, the ExperiencePlus! Italian tour leaders and I desired to develop a cycling tour that would combine the most exciting areas of Tuscany and Umbria (the green heart of Italy). This came to fruition last season with our new 8-day Cycling the Best of Southern Tuscany and 11-day Cycling the Best of Southern Tuscany Plus! Florence bicycling itineraries.
We all agreed that the first full ride of the tour should be to Assisi, the spiritual center of Umbria. A visit to Assisi provides an intriguing glimpse into the life of St. Francis – the Patron Saint of Italy and the founder of the Franciscan order. Our guided walking tour of the town features a visit to the Basilica di San Francesco, a World Heritage Site, to admire the incredible frescoes of artists Giotto and Cimabue.
Umbria has much to offer bicycling enthusiasts including lovely hilltop villages similar to those that have made Tuscany famous. A closer look reveals that Umbria is also home to amazing artigianato (handicrafts) such as the famous ceramics of Deruta, and its gastronomia (gastronomy) are unmatched. The region is known for strangozzi and umbricelli–two types of delicious homemade pasta traditionally served with a truffle or Ragù sauce, or tomato and Pecorino cheese depending on the season. Local cold cut specialties like Prosciutto di Norcia are also renowned in the area, along with fine lentils grown near Castelluccio that are often used in soups and side dishes. Umbria is considered, even by Italians, a truly authentic and culturally rich region.
Our bicycle journey includes my favorite highlights of Umbria and continues into Tuscany starting with an overnight in the town of Cortona made famous by Frances Mayes’, novel Under the Tuscan Sun. Cortona is a true medieval hill-top-town and as you pedal to the top you’ll understand the offensive and defensive advantages such a location has provided over the centuries. Celebrate your accomplishment and enjoy the mix of history and modern flavors this lovely city offers. I recommend a visit to the Etruscan Museum, and the Museo Diocesano with Fra Beato Angelico paintings (Annunciazione and Madonna Col Bambino to name a few). Also, a stroll along the medieval Via Iannelli and the Etruscan-Roman walls offers dramatic views of Lake Trasimeno where you can imagine Flaminius and Hannibal battling in 217 B.C. Don’t forget to relax, sit in the piazza, enjoy a glass of wine or espresso, and catch the sunset as it sinks beneath the walls of this romantic city.
Leaving Cortona we pedal into the vineyards of the Val di Chiana, a beautiful valley, to the village of Montepulciano, famous for its excellent red wine Nobile di Montepulciano. I love the towns we visit on this trip not only for their excellent food and wine, but because they are small jewels of architecture that present an opportunity to walk through history. Montepulciano is a quintessential Tuscan village, constructed at the top of a long ridge with clay hills, vineyards and forests below. It has also been an important political and economic hub through the centuries due to its strategic position at the crossroads of Arezzo and Chiusi (north to south) and Val d’Orcia and Lake Trasimeno (east to west).
After Montepulciano, we bicycle to Pienza where you can revel in the scent of artisanal Pecorino cheese as you approach the village. Enjoy this pint-size Renaissance town, a perfect example of early urban planning, with stunning views of the Orcia Valley. I consider the bicycle ride from Pienza to Montalcino and on to Siena a highlight of the tour. You’ll feel connected to an ancient past as you ride past clay hills and along small roads lined with cypress trees on the way to the 12th century, Abbazia di Sant’Antimo, and 14th century Monte Oliveto Maggiore Abbey.
For your stay in Siena I suggest you explore the town without a map and get lost among the small streets that connect Piazza del Campo (the famous Palio square) with the Duomo, Spedale Santa Maria della Scala, San Domenico and the many contrade or neighborhoods. Siena’s 17 contrade are all named for an animal or symbol and each participate in the Palio di Siena horse race. You’ll soon see how the Sienese have turned this biannual event (July 2 and August 16) into a year-round economic boon and cultural symbol as you walk through each neighborhood and see banners proudly displayed along with a myriad of souvenirs. The Palio is more than a horse race as there are also parades of drummers and flag throwers who work throughout the year at any important event including funerals, weddings, baptisms or church holidays.
Like many of our bicycle tours, we have a shorter itinerary (in this case 8 days) and a longer or Plus! option (11 days). The 8-day itinerary for this trip ends in Siena, so if you don’t have time to continue with us to Florence, I highly recommend you stay one more night to enjoy this unique town. For those on the 11-day trip we do enjoy two nights in Siena so you’ll have time to appreciate all that this intriguing city has to offer.
If you continue with us on the Plus! version of the tour you will cycle through what is considered classic Tuscany on our way to Florence. We’ll ride through the famous Chiantishire region of Tuscany, sip great red wines, taste the special cold cuts of the Macelleria Falorni, and stay in the main square of Greve in Chianti. Upon reaching Piazzale Michelangelo overlooking Florence, it is a beautiful yet bittersweet view as you realize that you have nearly completed your bicycle ride through two of Italy’s finest regions.
See what past customers have said about this trip on our review page.